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L-Tartaric acid

Base Information Edit
  • Chemical Name:L-Tartaric acid
  • CAS No.:87-69-4
  • Deprecated CAS:1336-18-1,8014-54-8,8059-77-6,1039646-76-8,1334703-49-9,1488329-53-8,2088032-42-0,2411406-12-5,138508-61-9,1039646-76-8,1334703-49-9,8014-54-8,8059-77-6
  • Molecular Formula:C4H6O6
  • Molecular Weight:150.088
  • Hs Code.:29181200
  • European Community (EC) Number:201-766-0
  • ICSC Number:0772
  • NSC Number:759609
  • UNII:4J4Z8788N8,W4888I119H
  • DSSTox Substance ID:DTXSID8023632
  • Nikkaji Number:J31.839F
  • Wikipedia:Tartaric acid,Tartaric_acid
  • Wikidata:Q18226455
  • NCI Thesaurus Code:C47744
  • RXCUI:37578
  • Metabolomics Workbench ID:37519
  • ChEMBL ID:CHEMBL1236315
  • Mol file:87-69-4.mol
L-Tartaric acid

Synonyms:(R*,R*)-(+-)-2,3-dihydroxybutanedioic acid, monoammonium monosodium salt;aluminum tartrate;ammonium tartrate;calcium tartrate;calcium tartrate tetrahydrate;Mn(III) tartrate;potassium tartrate;seignette salt;sodium ammonium tartrate;sodium potassium tartrate;sodium tartrate;stannous tartrate;tartaric acid;tartaric acid, ((R*,R*)-(+-))-isomer;tartaric acid, (R*,S*)-isomer;tartaric acid, (R-(R*,R*))-isomer;tartaric acid, (S-(R*,R*))-isomer;tartaric acid, ammonium sodium salt, (1:1:1) salt, (R*,R*)-(+-)-isomer;tartaric acid, calcium salt, (R-R*,R*)-isomer;tartaric acid, monoammonium salt, (R-(R*,R*))-isomer;tartrate

Suppliers and Price of L-Tartaric acid
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • Chem-Impex
  • L(+)-Tartaric acid ≥ 99.0% (Titration)
  • 1KG
  • $ 35.00
  • Chem-Impex
  • L(+)-Tartaricacid,≥99.0%(Titration),ACSreagent ≥99.0%(Titration)
  • 100G
  • $ 13.50
  • Ambeed
  • (2R,3R)-2,3-Dihydroxysuccinicacid 98%
  • 500g
  • $ 11.00
  • Ambeed
  • (2R,3R)-2,3-Dihydroxysuccinicacid 98%
  • 100g
  • $ 6.00
  • Ambeed
  • (2R,3R)-2,3-Dihydroxysuccinicacid 98%
  • 25g
  • $ 5.00
  • Ambeed
  • (2R,3R)-2,3-Dihydroxysuccinicacid 98%
  • 1kg
  • $ 20.00
  • Alfa Aesar
  • L-(+)-Tartaric acid, ACS
  • 2kg
  • $ 225.00
  • Alfa Aesar
  • L-(+)-Tartaric acid, 99%
  • 100g
  • $ 15.80
  • Alfa Aesar
  • L-(+)-Tartaric acid, 99%
  • 500g
  • $ 33.70
  • Alfa Aesar
  • L-(+)-Tartaric acid, ACS
  • 100g
  • $ 29.40
Total 351 raw suppliers
Chemical Property of L-Tartaric acid Edit
Chemical Property:
  • Appearance/Colour:white crystals 
  • Vapor Pressure:4.93E-08mmHg at 25°C 
  • Melting Point:170-172 °C(lit.) 
  • Refractive Index:12.5 ° (C=5, H2O) 
  • Boiling Point:399.3 °C at 760 mmHg 
  • PKA:2.98, 4.34(at 25℃) 
  • Flash Point:209.4 °C 
  • PSA:115.06000 
  • Density:1.886 g/cm3 
  • LogP:-2.12260 
  • Storage Temp.:Store at RT. 
  • Solubility.:H2O: soluble1M at 20°C, clear, colorless 
  • Water Solubility.:1390 g/L (20 ºC) 
  • XLogP3:-1.9
  • Hydrogen Bond Donor Count:4
  • Hydrogen Bond Acceptor Count:6
  • Rotatable Bond Count:3
  • Exact Mass:150.01643791
  • Heavy Atom Count:10
  • Complexity:134
Purity/Quality:

99% *data from raw suppliers

L(+)-Tartaric acid ≥ 99.0% (Titration) *data from reagent suppliers

Safty Information:
  • Pictogram(s): IrritantXi 
  • Hazard Codes:Xi 
  • Statements: 36/37/38-41 
  • Safety Statements: 26-36-37/39-36/37/39 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Other Classes -> Organic Acids
  • Canonical SMILES:C(C(C(=O)O)O)(C(=O)O)O
  • Isomeric SMILES:[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
  • Recent NIPH Clinical Trials:Unraveling of neural basis of voluntary cough and cough reflex
  • Inhalation Risk:Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
  • Effects of Short Term Exposure:Corrosive. The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation of the aerosol may cause lung oedema. The effects may be delayed. Medical observation is indicated.
  • Natural Occurrence L-Tartaric acid (L-TA) is a weak organic acid found naturally in various fruits, including grapes, tamarind, and citrus fruits.
  • Chemical Composition and Properties L-Tartaric acid is also known as 2,3-dihydroxysuccinic acid. It contains carboxylic acid and hydroxyl groups, making it a versatile compound. It is considered a safe and biodegradable substance.
  • Uses in Industries L-Tartaric acid finds widespread use in brewing, pharmaceutical, and food industries due to its natural sourcing and favorable properties. It serves as a chiral recognition material and has applications in asymmetric catalysis, chiral extraction, chiral chromatography, and electrophoretic separation.
  • Sprout Suppressing Agent L-Tartaric acid demonstrates effectiveness as a sprout-suppressing agent. It exhibits allelopathic activities and plays a role in the synthesis of bioactive molecules and antimicrobial agents.
  • Use in Drug Formulations L-Tartaric acid has been studied as a model drug and coformer in co-amorphous systems and solid dispersions. It is explored for its potential to enhance the solubility of active pharmaceutical ingredients (APIs).
  • General Description **Conclusion on L(+)-Tartaric Acid:** L(+)-Tartaric acid, a naturally occurring chiral dicarboxylic acid, serves as a versatile and cost-effective chiral pool source in asymmetric synthesis. It is widely utilized in the preparation of chiral ionic liquids (CILs), where its derivatives, such as pyrrolidinium salts, exhibit potential for chiral recognition and applications in asymmetric catalysis or solvents. Additionally, L(+)-tartaric acid acts as a key precursor in the stereocontrolled synthesis of complex molecules, including β-lactams and higher-carbon sugars, highlighting its importance in enantioselective transformations and the development of novel chiral synthons. Its renewable nature and structural rigidity further enhance its utility in designing functional materials and bioactive compounds. *(Note: The second abstract provided no relevant content on L(+)-tartaric acid beyond its use as a starting material, so the conclusion focuses on insights from the first and third abstracts.)*
Technology Process of L-Tartaric acid

There total 234 articles about L-Tartaric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Refernces Edit

Total syntheses of penicillanic acid s,s-dioxide and 6-aminopenicillanic acid using(benzyloxy)nitromethane

10.1021/jo00304a024

The research focuses on the stereocontrolled total syntheses of penicillanic acid S,S-dioxide (10) and 6-aminopenicillanic acid (26) derived from (S)-aspartic acid and (R,R)-tartaric acid, respectively. The study's key steps involve the preparation and cyclization of nitroalkenes 8 and 23, with the reaction of these compounds with tetrabutylammonium fluoride followed by ozone and DBU yielding the bicyclic P-lactams 9 and 24, which are then transformed into the target penicillanic acid derivatives 10 and 26. The research concludes that (benzyloxy)nitromethane is a highly useful reagent in β-lactam chemistry, and the nitroalkene ring closure strategy is efficient and effective for preparing polyfunctional bicyclic β-lactams, with potential general applicability for constructing novel β-lactam systems.

Novel L-tartaric acid derived pyrrolidinium cations for the synthesis of chiral ionic liquids

10.1055/s-0028-1087950

The research presents the synthesis of novel chiral ionic liquids (CILs) based on L-(+)-tartaric acid, leveraging its low cost and renewability as a chiral pool source. The study's main content involves a two-step synthesis strategy: first, reacting L-tartaric acid with benzylamine to form pyrrolidindione, followed by reduction with LiAlH4 to obtain benzylpyrrolidine. Subsequent quaternization with benzyl or n-dodecyl bromide under conventional or microwave heating yielded the desired chiral pyrrolidinium salts. The synthesized compounds were characterized by their melting points, and anion exchange was performed to obtain different ionic liquids. The researchers also examined the crystallographic structures of selected compounds to understand the absence of hydrogen-bonding interactions between cations, which contributed to the reduced melting points. The chiral recognition ability of these ionic materials was evaluated through NMR spectroscopy, observing the interaction between the synthesized cations and Mosher acid anion, which indicated the formation of diastereomeric salts. This research provides a foundation for further investigation into the potential of these CILs as solvents, catalysts, or ligands in asymmetric synthesis.

Higher-carbon sugars: a novel approach

10.1016/0008-6215(86)85018-2

The research discusses a novel approach to synthesizing natural compounds containing α,β-unsaturated δ-lactones using carbohydrate precursors. The purpose of this study was to develop chiral synthons with the L configuration, which are essential for the enantiospecific synthesis of these compounds. The researchers successfully prepared 2,3-dideoxy-4,6,7,8-tetra-O-methyl-D-glycero-D-galacto-2-enono-1,5-lactone (1) through a series of chemical reactions starting from L-tartaric acid. Key chemicals used in the process included ethanethiol-hydrochloric acid, sodium hydride, methyl iodide, mercury(II) oxide-mercury(II) chloride, palladium on carbon catalyst, and toluene-p-sulphonic acid. The synthesis involved several steps, such as the preparation of 3-O-benzyl-D-glucose diethyl dithioacetal, its methylation, transacetalization, catalytic hydrogelation, and finally, the Wittig reaction to obtain the desired lactone. The study concluded with the successful preparation of the target lactone and the observation that the extension of these sequences for the preparation of other lactones with extended chains is feasible and under investigation.

Preparative separation of tetrahydrofurfurylamine enantiomers

10.1134/S1070428007120123

D. M. Musatov et al. detail a method for separating the enantiomers of tetrahydrofurfurylamine on a preparative scale using fractional crystallization of diastereoisomeric salts with natural L-tartaric acid. Tetrahydrofurfurylamine is a significant compound used in the synthesis of various medical agents, including diuretics, enzyme inhibitors, analgesics, neurotropic drugs, and anticarcinogenic agents. The study reports the isolation of (R)-tetrahydrofurfurylamine with a yield of 68% and an optical purity of over 98.5% as determined by HPLC. The separation process involved dissolving L-tartaric acid and racemic tetrahydrofurfurylamine in a mixture of water and acetone, followed by crystallization and recrystallization steps. The (R)-enantiomer was obtained with high purity, while the mother liquor yielded the (S)-enantiomer with 79% enantiomeric purity.

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